Synthesis and isomerization of acridine substituted 1,3-thiazolidin-4- ones and 4-oxo-1,3-thiazolidin-5-ylidene acetates. An experimental and computational study

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F18%3A73590666" target="_blank" >RIV/61989592:15310/18:73590666 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0022286017313893" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0022286017313893</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2017.10.046" target="_blank" >10.1016/j.molstruc.2017.10.046</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and isomerization of acridine substituted 1,3-thiazolidin-4- ones and 4-oxo-1,3-thiazolidin-5-ylidene acetates. An experimental and computational study

Popis výsledku v původním jazyce

Acridine thiosemicarbazones 3aeg, obtained through a two-step reaction between aromatic isothiocyanates and hydrazine followed by the treatment with acridin-9-carbaldehyde, in reaction with bifunctional reagents; methyl bromoacetate (MBA) and diethyl acetylenedicarboxylate (DEAD) afforded acridin-thiazolidinone derivatives 4aeg and 7aef and not their regioisomers 6aeg and 9aef. Derivatives 4aeg and 7aef exhibit ZC2N6EN7C8 configuration. Upon standing in DMSO-d6 the thiazolidinones 4aeg and 7aef spontaneously isomerized into ZC2N6ZN7C8 isomers 5aeg and 8aef to give a mixture of the both stereoisomers. All compounds were fully characterized by multinuclear NMR, mass spectrometry (MS) and X-ray crystal structure of 4b is also described. X-ray diffraction study revealed that the representative compound 4b crystallized in the monoclinic crystal system with the C2/c space group and Z ¼ 4. Intramolecular C10eH10/N-7 hydrogen bond between the acridine proton H-10 and nitrogen N-7 of linker existed. This hydrogen bond is responsible for the E isomerism on C-8 atom which was observed in the NMR experiments. Quantum-chemical calculations and NOESY experiments confirmed ZC2N6ZN7C8 configuration of the transformed stereoisomers 5aeg and 8aef.

Název v anglickém jazyce

Synthesis and isomerization of acridine substituted 1,3-thiazolidin-4- ones and 4-oxo-1,3-thiazolidin-5-ylidene acetates. An experimental and computational study

Popis výsledku anglicky

Acridine thiosemicarbazones 3aeg, obtained through a two-step reaction between aromatic isothiocyanates and hydrazine followed by the treatment with acridin-9-carbaldehyde, in reaction with bifunctional reagents; methyl bromoacetate (MBA) and diethyl acetylenedicarboxylate (DEAD) afforded acridin-thiazolidinone derivatives 4aeg and 7aef and not their regioisomers 6aeg and 9aef. Derivatives 4aeg and 7aef exhibit ZC2N6EN7C8 configuration. Upon standing in DMSO-d6 the thiazolidinones 4aeg and 7aef spontaneously isomerized into ZC2N6ZN7C8 isomers 5aeg and 8aef to give a mixture of the both stereoisomers. All compounds were fully characterized by multinuclear NMR, mass spectrometry (MS) and X-ray crystal structure of 4b is also described. X-ray diffraction study revealed that the representative compound 4b crystallized in the monoclinic crystal system with the C2/c space group and Z ¼ 4. Intramolecular C10eH10/N-7 hydrogen bond between the acridine proton H-10 and nitrogen N-7 of linker existed. This hydrogen bond is responsible for the E isomerism on C-8 atom which was observed in the NMR experiments. Quantum-chemical calculations and NOESY experiments confirmed ZC2N6ZN7C8 configuration of the transformed stereoisomers 5aeg and 8aef.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/LO1204" target="_blank" >LO1204: Udržitelný rozvoj výzkumu v Centru regionu Haná</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

JOURNAL OF MOLECULAR STRUCTURE

ISSN

0022-2860

e-ISSN

—

Svazek periodika

1154

Číslo periodika v rámci svazku

FEB

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

13

Strana od-do

152-164

Kód UT WoS článku

000418212000019

EID výsledku v databázi Scopus

2-s2.0-85031714368